4-Bromo-1-fluoro-2-nitrobenzene → 4-Bromo-7-fluoroindole

HRID 2278390Notes

Reaction equation

HRID 2278390 reaction equation
[CH:1]([Mg]Br)=[CH2:2].[N+:5]([C:8]1[CH:9]=[C:10]([Br:15])[CH:11]=[CH:12][C:13]=1[F:14])([O-])=O>C1COCC1>[Br:15][C:10]1[CH:11]=[CH:12][C:13]([F:14])=[C:8]2[C:9]=1[CH:1]=[CH:2][NH:5]2

Participants

4

Reactant 2

HCID 27363284-Bromo-1-fluoro-2-nitrobenzeneHCID 178418507HCID 178418507, compound

Product 1

HCID 38225414-Bromo-7-fluoroindoleYield 23.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At −40° C., vinylmagnesium bromide (300 mL of 1.0M solution in THF, 300 mmol) was added dropwise to a solution of 3-nitro-4-fluoro-bromobenzene (22 g, 100 mmol) in THF (700 mL). After 1 h at −40° C., the mixture was quenched by aqueous NH4Cl solution and extracted by EtOAc. The organic layer was dried over Na2SO4 and concentrated to give the crude product which was purified by silica gel column chromatography affording 4-bromo-7-fluoro-1H-indole (5 g, 23.3%).

Workup

  1. customthe mixture was quenched by aqueous NH4Cl solution
  2. extractionextracted by EtOAc
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customto give the crude product which
  6. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-67a5de6ccea04a9ea54cc5fd323bfe21
Source dataset
uspto-grants-2015_09
Patent number
US09133180B2

Reaction notes

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